3-(Trifluoromethyl)phenol → 8-Nitro-4-(3-(trifluoromethyl)phenoxy)quinoline

HRID 1469734노트

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HRID 1469734 반응식
Cl[C:2]1[C:11]2[C:6](=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[F:15][C:16]([F:25])([F:24])[C:17]1[CH:18]=[C:19]([OH:23])[CH:20]=[CH:21][CH:22]=1.C([O-])([O-])=O.[K+].[K+]>CC#N>[N+:12]([C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[N:5]=[CH:4][CH:3]=[C:2]2[O:23][C:19]1[CH:20]=[CH:21][CH:22]=[C:17]([C:16]([F:15])([F:24])[F:25])[CH:18]=1)([O-:14])=[O:13]

참가 물질

5

반응물 3

HCID 73763-(Trifluoromethyl)phenolHCID 11430Potassium CarbonateHCID 6104404-Chloro-8-nitroquinoline

생성물 1

HCID 866922328-Nitro-4-(3-(trifluoromethyl)phenoxy)quinoline수율 37.4%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
100 °C

실험 절차

A suspension of 4-chloro-8-nitroquinoline (200 mg, 0.96 mmol), 3-(trifluoromethyl)phenol (250 mg, 1.54 mmol), K2CO3 (414 mg, 2.99 mmol) in CH3CN (2 mL) was heated in a sealed tube at 100° C. for 8 h. Then the reaction mixture was quenched with water and was extracted with EtOAc. The organic layer was washed with brine, separated, dried, filtered and concentrated. The residue was purified by column chromatography to afford 120 mg of the title product. 1H NMR (300 MHz, DMSO d6): δ 8.83 (d, J=5.4 Hz, 1H), 8.60-8.57 (d, J=8.4 Hz, 1H), 8.36 (d, J=6.9 Hz, 1H), 7.85-7.73 (m, 5H), 6.87 (d, J=5.4 Hz, 1H).

후처리

  1. customThen the reaction mixture was quenched with water
  2. extractionwas extracted with EtOAc
  3. washThe organic layer was washed with brine
  4. customseparated
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-6af45d456dd64c779d5bff0e51af0524
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006257B2

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